I really hope that it can "free" up my schedule so that I don't have to rely on a 9-5 to support my life. 

It seems like you really need to go the whole hog and buy a $200-$300K property, scrape and rebuild for $400K or so, and sell for ~$1M to see the true margin that makes things repeatable and scalable.At least, that's what I'm seeing in terms of a strategy that does not rely on the red hot appreciation of the last few years to carry values over a given 6-12 month period.

I feel like I need to know more about how houses work in order to do this instead of solely relying on bringing a contractor out.

We got a great jump on this I feel like with the videos, workbooks, forms, checklists, etc that we provide, however I will be relying on the people in the course/mastermind to help us craft the future of the product/community as well. 

After taxes and management fees, the owner can get 10% + gain directly in the pocket without doing anything.Sharing economy websites like Airbnb or VRbo are a great platform but you should not rely only on this channel.

Flips rely on access to cash and buy and holds sometimes encumber that cash.

So you have to think outside the box and put together lead sources that translates to "motivation."

From your description though, until there is further appreciation and/or savings input from you, you'll still be relying on private loans for each fresh purchase UNTIL their refi.The second biggest hurdle is: finding deals that also still cash flow positively, even at 70% leverage (so that eventually, you WILL be able to borrow conventionally from then on).

He may not have noticed that you live in Santa Ana, thus rely on property management companies. 

Once you have a license, you can go off your gut based on your own market versus relying on what others think.